The Cumberland River in Tennessee and Kentucky offers a diverse range of paddling experiences, from urban excursions to remote wilderness floats. In downtown Nashville, a popular and beginner-friendly route is the 3-mile, one-way paddle from the Shelby Park Boat Ramp in East Nashville to Nissan Stadium. This urban section provides unique views of the Nashville skyline, passing under several bridges. The Shelby Park Boat Ramp is a paved public access point with free parking, though trailer parking can fill on busy weekends. Outfitters in Nashville offer kayak and stand-up paddleboard rentals and guided services for this route, which typically takes about one hour of paddling time. This area is shared with larger commercial and recreational boats, requiring paddlers to be alert to traffic.

Upstream in Kentucky, the river's character changes significantly. The section upstream of Cumberland Falls, within the Daniel Boone National Forest, is a remote and scenic 17-mile stretch featuring shoals and mild Class I and II whitewater rapids. This area is known for its rugged hills, large boulders, and a more challenging, technical paddle, especially at lower water levels where dragging over shoals may be necessary. Ideal paddling flows are between 500 and 1,100 cubic feet per second, with higher flows creating more challenging conditions. Access points for this remote float include the Redbird Boat Ramp on KY 478. Another distinct area is the first 16 miles below Wolf Creek Dam at Lake Cumberland, which is known for a powerful current when the dam is generating electricity, but can be ideal for small boats during low water flows. This section includes several mild shoals suitable for beginners to develop skills. Paddlers must wear a personal flotation device at all times on Kentucky waters. The river is home to wildlife such as blue herons, turtles, and kingfishers, particularly noted along the Nashville route.